Coastal Cowgirl: Dance Party in Aisle Five

A beach reset in Naples, Florida, takes an unexpected turn.

Only in Naples can you buy cucumbers, order a steak dinner, and dance to DJ music under the same roof.

I went to Naples looking for a coastal reset.

Sunshine. A little shopping. A walk along the Gulf. Maybe a nice glass of wine.

Nothing dramatic.

And for most of the trip, Naples cooperated.

Tin City

After the three‑hour drive, I checked into Hyatt House Naples/5th Avenue, dropped my bags, and wandered through the underpass to Tin City for lunch at Pinchers.

Grilled grouper tacos, fries, coleslaw, iced tea — enough food that half of lunch became dinner.

By late afternoon, thunder rolled in, so I surrendered to the weather and headed to the hotel’s Latitude 26 for happy hour. Sometimes adventure means knowing when to stop.

Docks on Fifth Marina

The hotel sits along the Gordon River, where palms frame a marina dotted with boats and soft reflections.

Following the deck leads to the Cabana Bar, K‑Rico Mexican Grill, and Tavern on the Bay.

The next morning, sunrise filtered through the palms, washing the marina in gold and coral. I carried my coffee outside and watched Naples wake up.

Not a bad way to start a day.

The Parking Meter From Hell

Wednesday morning was beautiful, so I drove to Lowdermilk Park — a Naples beach I’d never visited. Finding the beach was easy. Parking was where things got interesting.

I walked over to the pay station, intending to purchase an hour for $5.  I made my selections, paid, and walked away.

A few minutes later, I looked at the receipt.

$51.75.

I stared at it.

Apparently, I had not purchased an hour of beach parking. I had purchased what appeared to be an entire day of Naples beachfront real estate.

I went back to the machine and hit cancel, hoping to reverse my accidental contribution to the Naples parking fund.

The charge had already been approved.

I called the city parking line. The woman who answered was extremely pleasant as she explained they were unable to issue refunds. She suggested I dispute the charge with my credit-card company.

So that was that.

I spent a grand total of thirty-five minutes at Lowdermilk Park.

At that rate, I believe I briefly became the highest-paying beachgoer in Naples.

Lowdermilk itself was lovely — wide beach, paved parking, and Flip Flops, a beachfront pavilion serving breakfast, lunch, and coffee.

Seats along the railing overlook the Gulf.

Beautiful beach. Expensive lesson.

Remembering Naples

From there, I headed toward Fifth Avenue.

It had been four years since my last visit, and I’d forgotten how pretty downtown Naples is. Restaurants, galleries, and shops spill onto the side streets, giving the whole area that postcard quality Naples does so well.

I wandered into Art on Fifth Ave Naples, exercised remarkable financial discipline, and left without buying anything.

Eventually iced coffee became a priority, so I crossed over to 5th Avenue Coffee Co. & 6th Street Diner.

The iced coffee was one of the best I’ve ever had. If I lived locally, this would become a problem.

Third Street brought me to Tommy Bahama — a much larger store than my local store at Disney Springs. A sales associate proudly pointed out that this was the original location.

Then I discovered the Tommy Bahama restaurant next door. Another entry on the return‑trip list.

My relaxing little getaway was quietly becoming reconnaissance for the next one.

But Naples still had a surprise waiting.

A Grocery Store Walks Into a Nightclub

About twenty-five minutes later, I arrived at Seed to Table. I knew it was a grocery store. That description turned out to be wildly inadequate.

Seed to Table is part of the Oakes Farms family of businesses, with much of its produce grown on Oakes Farms acreage in Southwest Florida. That may explain the attention given to its produce displays.

Seed to Table is enormous — food stations offering sushi, seafood, steaks, tacos, and cheesesteaks line the perimeter. Wine and cheese areas. Bars. Restaurants.

There is an upstairs dining level with a giant indoor tree rising through the center.

A glowing neon sign announces Alfie’s Tequila & Cocktail Bar.

And, apparently, you can grocery shop while sipping wine.  Suddenly Publix seemed terribly underdressed.

Dining tables sit throughout the main level, including one booth tucked inside what looks like an enormous wine barrel.

I walked upstairs, found a high‑top table, and ordered the Southwest Chicken Salad. The portion looked designed for a small committee.

Then I noticed a sign on the stairwell.

Girls Night Out. 8–10 p.m.

At a grocery store.

Obviously, further investigation was required.

Girls’ Night Out – Naples Style

By eight o’clock, DJ Messina was playing dance music.

The regular tables and chairs near the upstairs railing had been moved aside to create more room.

Women could walk up to the bar and order free drinks.

The main bar was sectioned off and lined with male patrons.

Downstairs, people were dining at tables. Others were pushing carts through grocery aisles.

Meanwhile, upstairs women were dancing to music from the ‘80s and ‘90s.

Every so often I looked over the railing and smiled. A few shoppers danced their way through the aisles. At one point, a conga line wound past the produce displays.

The lettuce watched. The cucumbers judged. The eggplants posed like they were waiting for a casting call.

It was impossible not to appreciate the absurdity of it.

Where else can you order a steak dinner, buy groceries, sip a cocktail and hit the dance floor without ever leaving the building?

Even the produce seemed ready for a close‑up — cucumbers arranged neatly in wooden baskets, eggplants and peppers styled rather than stocked.

And one refrigerated wall arranged in blocks of color like someone hired an art director for the vegetables.

Some stores stock produce. Seed to Table stages it.

The energy kept building, but after about an hour I decided to head back toward downtown Naples before the next round of storms. On the drive, I passed another Oakes Farms market and made yet another mental note for another day.

Naples now requires a sequel.

Final Thoughts

My final morning was quiet. After an early breakfast, I took a walk around the marina and decided not to cram anything else into the trip.

The three-hour drive home was still ahead of me.

There had been no major travel drama.

Sometimes a trip doesn’t need to become a grand story.

Sometimes the reset is the story.

5th Avenue Storefront Decorative Pot

Part of the Coastal Cowgirl Series

Coastal Cowgirl: Naples, Florida

When I first moved to Florida in May, 2022, I lived in an apartment while I searched for my new home. I explored the state like a woman who had been handed a map, a full tank of gas, and absolutely no reason to stay home.

Every week brought another town, another “maybe I live here now” moment. In each place, I explored what life might look like there—but most importantly, I evaluated riding options, boarding stables for Rosie, and nearby hiking trails.

I began on the Gulf Coast in Naples—the polished, palm-lined, rosé-at-lunch version of Florida.

Naples offered everything I needed for a soft landing: beaches, shopping, and the kind of Gulf breezes that make you forget you once survived life in the Sonoran Desert.

When I relocated from Phoenix, I traded blazing, bone-dry heat for something softer—still hot but wrapped in humidity.

I grew up on the East Coast, so the air here felt more like home than anything the desert ever offered.

Life Beneath the Flight Path

I stayed at the Hyatt House on 5th Avenue, perfectly positioned along the Gordon River Marina and walking distance to Tin City. It was the ideal base.

Well… ideal except for one tiny detail.

The room I booked overlooked the river from the back of the hotel—which, as I soon learned, sits directly beneath the flight path for Naples Airport.

One afternoon, I was sitting on my balcony, relaxing like a woman who had finally found her Florida calm. The sky was blue, the air was warm, the river was quiet…

And then— a loud whoosh overhead.

A jet came over so low I felt like I could read the pilot’s name tag.

The first time it happened, I didn’t just flinch—I instinctively ducked.  That first one spooked me harder than a horse encountering a plastic grocery bag.

Still, Naples had me hooked.

A Coastal Cowgirl Needs a Horse

No Florida chapter of mine would be complete without a horseback ride, so I found a local stable and joined a group trail ride through the wooded, sandy paths of Golden Gate Estates.

The horses were steady, the guide was friendly, and the trails felt like stepping into a quieter, wilder version of Naples.

It was the perfect blend of coastal and cowgirl—palm trees, pine flatwoods, and the soft thud of hooves on sugar sand.

As I drove through Golden Gate Estates, I caught myself daydreaming—the kind of daydream where you buy a few acres, build a barndominium, and give your horse the kind of at-home life that makes both of you happy.

Then reality arrived in the form of a single word: Hurricanes.

At the time, I had absolutely no hurricane experience.

The last thing I wanted was to find myself trying to evacuate a horse while half of South Florida attempted to leave at the same time.

I had evacuated horses ahead of a wildfire in Arizona. But I knew those roads and it wasn’t a mass exodus.

Standing in Golden Gate Estates, I realized I wasn’t ready to repeat that experience with hurricanes.

That was the moment I knew Naples—and other beach communities—could be my escape, my coastal reset, but not my home base.

So I stayed in Central Florida, where hurricanes remain a possibility but the logistics are kinder, and I let the coasts become my playground instead of my responsibility.

Hiking the Wild Side of Naples

Every place I’ve lived, I’ve adjusted my riding and hiking to the local terrain.

Delaware and the Jersey Shore offered parks and long beach walks. Arizona traded shade for red rock, elevation gains, and desert washes. Florida introduced me to mangroves, pine flatwoods, and wetlands.

The terrain changed; the daily mileage simply found a new backdrop.

As an avid hiker, I normally cover several miles a day, six days a week, so Naples’ trails and boardwalks were an easy invitation.

I relied heavily on the AllTrails app to help me find routes that wouldn’t leave me lost, isolated, or starring in a local news segment.

My first hike was the Gordon River Greenway, a peaceful 2.8-mile out-and-back trail combining paved pathways and elevated boardwalks through mangroves and shaded wetlands.

From there, I ventured into Florida’s largest state park: Fakahatchee Strand Preserve.

The Big Cypress Bend Boardwalk stretches 2,500 feet through spectacular swamp scenery before ending at an observation deck overlooking an alligator pond.

It’s the kind of place where you half expect a nature documentary narrator to emerge from the trees.

I also hiked a section of the Florida Trail along East Main Tram, an easy four-mile out-and-back route following former logging roads.

Parts were muddy but manageable, and thanks to the wisdom of previous hikers posting on AllTrails, I wore waterproof shoes instead of discovering the mud the hard way.

Tin City After Dark

No Naples visit would be complete without a stop at Tin City, conveniently located within walking distance of the Hyatt.

The shops were fun. The waterfront was beautiful.

But the real entertainment arrived after dark.

One evening, as I dined on the open-air deck, a party boat returned to the dock carrying passengers who were enthusiastically singing to the music.

They were blissfully happy, rum-punch powered, and ready to toast anything that wasn’t nailed down.

My favorite was the final passenger to leave the boat.

She was still dancing to music that no longer existed.

The crew attempted to guide her down the gangway.

One even tried dancing her toward the exit.

Eventually, she was escorted safely onto the dock, where she continued performing for the benefit of waterfront diners.

Last I saw, she was twirling toward the nearest bar like an adorable dancing diva.

Not Every Place Is Meant to Be Home

The best part of Naples has always been its effortless elegance.

The soft Gulf light and the calm water. The breezes that feel like an exhale.

Naples never seems to demand attention. It simply exists, confident in what it is, and that quiet existence is part of its charm.

When I was searching for a place to call home, Naples taught me something important: not every place you love is meant to be where you live.

Some places become escapes, others become the places you return to when life feels too loud.

Every visit reminds me why it remains one of my favorite coastal escapes—a place where nature, adventure, and coastal elegance come together effortlessly.

Part of the Coastal Cowgirl Series